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CAS No. : | 4130-42-1 | MDL No. : | MFCD00017366 |
Formula : | C16H26O | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | BVUXDWXKPROUDO-UHFFFAOYSA-N |
M.W : | 234.38 | Pubchem ID : | 20087 |
Synonyms : |
|
Signal Word: | Danger | Class: | 9 |
Precautionary Statements: | P501-P273-P260-P270-P264-P280-P391-P314-P337+P313-P305+P351+P338-P301+P312+P330 | UN#: | 3077 |
Hazard Statements: | H302-H319-H372-H410 | Packing Group: | Ⅲ |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With potassium hydroxide; potassium hexacyanoferrate(III) In hexane; water monomer at 23℃; for 1h; Inert atmosphere; | |
84% | With potassium hexacyanoferrate (III); potassium hydroxide In hexane; water monomer at 20 - 25℃; for 2h; | General Procedure B: Preparation of para-quinone methides from 4-benzylphenols General procedure: Following a literature procedure,[1] the requisite 4-benzylphenol (1.0 equiv.), KOH (4.2equiv.) and K3Fe(CN)6 (4.0 equiv.) in hexane/H2O (1:1) was vigorously stirred for 2 h at rtbefore being diluted with EtOAc (× 1) and washed with distilled water (× 4). The combinedorganic layers were dried over anhydrous Na2SO4, and the filtrate concentrated in vacuo. Thecrude material was purified by flash silica column chromatography to give the desired paraquinonemethide. |
69% | With potassium hydroxide; potassium hexacyanoferrate(III) In hexane; water monomer at 20℃; for 6h; Inert atmosphere; |
With potassium hexacyanoferrate(III); benzene | ||
With potassium hydroxide; potassium hexacyanoferrate(III) | ||
With sodium peroxodisulphate; sodium ferrocyanide decahydrate; sodium hydroxide In hexane; water monomer for 4h; Inert atmosphere; | ||
With sodium peroxydisulfate; sodium ferrocyanide decahydrate; sodium hydroxide In hexane; water monomer for 4h; Inert atmosphere; | ||
With potassium hydroxide; potassium hexacyanoferrate(III) In water monomer at 23℃; for 1h; Inert atmosphere; | 2.1.3 General procedure for synthesis of2,6-di-tert-butyl-4-ethylidenecyclohexa-2,5-dien-1-one Potassium ferricyanide (4.0 equiv.) and potassium hydroxide (4.2 equiv.) in waterwere added in one portion to a solution of 2,6-di-tert-butyl-4-ethylphenol (1.0 equiv.)in hexane under argon. The reaction mixture was stirred vigorously for 1h at 23°C.The aqueous layer was separated and extracted with hexanes. The combined organiclayers were washed with brine and dried over anhydrous sodium sulfate. The solidswere removed by filtration and the solution was concentrated by rotary evaporation.The residue was purified by silica gel flash column chromatography to affordcorresponding product 2y. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With Isopropylbenzene; Cumene hydroperoxide; cobalt(II) o-phthalate at 80 - 100℃; Behandeln mit Luft; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With Isopropylbenzene; air; Cumene hydroperoxide; cobalt(II) o-phthalate at 80 - 100℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydroxide; ethanol at 225℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sulfuric acid | ||
With sulfuric acid at 70℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | With cesium hydroxide; oxygen; triethyl phosphite In dimethyl sulfoxide at 25℃; for 12h; | 2.2 General procedure for aerobic oxidative synthesisof p-quinols from multi-alkyl phenols General procedure: CsOH (7.5 mg, 0.05 mmol), P(OEt)3 (167 mg, 1.0 mmol), 3(0.5 mmol) were added to a 25 mL Schlenk tube with a magnetic bar under O2. DMSO (2.0 mL) was added and then the mixture was stirred at room temperature (25 °C) under O2 (1 atm) for 12 h. The solution was then diluted with ethyl acetate (10 mL), washed with brine (3 mL), extracted with ethyl acetate (3×5 mL), dried over anhydrous Na2SO4, filtered, and evaporated under vacuum. The crude reaction mixture was purified by column chromatographyon silica gel to get the desired product 4.. |
83% | With perchloric acid; water; lead dioxide In acetone for 0.133333h; | |
With potassium <i>tert</i>-butylate; oxygen |
(electrochemical oxidation); | ||
With oxygen In methanol Ambient temperature; | ||
Multi-step reaction with 2 steps 1: aq. KOH, O2 / ethanol / 14 h / 0 - 5 °C 2: aq. KI, aq. acetic acid |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
(i) KOtBu, tBuOH, (ii) NaH, PE; Multistep reaction. Further byproducts given; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
(i) KOtBu, tBuOH, (ii) /BRN= 505934/; Multistep reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 78% 2: 2 % Chromat. | at 270℃; for 24h; reaction time 8 h; | |
1: 2 % Chromat. 2: 78% | at 270℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | With 2,8-dibromo-5,5-difluoro-1,3,7,9-tetramethyl-10-phenyl-5H-dipyrrolo[1,2-c:2′,1′-f ][1,3,2]diazaborinin-4-ium-5-uide; oxygen In 1,4-dioxane for 6h; Irradiation; | |
70% | With potassium hydroxide; oxygen In ethanol; water | |
With potassium hydroxide; oxygen In ethanol at 0 - 5℃; for 14h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With <CoL3>; oxygen 1.) CH2Cl2, 0 deg C, 2-4 h; 2.) CH2Cl2; Yield given. Multistep reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With phosphotungstic acid In acetic acid at 140℃; other temperatur; catalysis of dealkylation of 2,6-di-tert-butylphenol derivatives by heteropoly acids; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Heating; Yield given. Yields of byproduct given; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
rate constant of the disproportionation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With oxygen Multistep reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydroxide; sodium tetrahydroborate In methanol at 30℃; for 48h; Yield given. Yields of byproduct given; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With trimethyl phosphite; sulfuryl dichloride at 3℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 28% 2: 43% | In N,N-dimethyl-formamide for 0.616667h; electrolysis, n-Bu4NClO4; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | With lithium aluminium tetrahydride In tetrahydrofuran; chlorobenzene for 1h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Rk. mit dem Peroxy-Radikal von Cumol in EtOH bei 60grad <Inhibierung der durch Azoisobutyrodinitril initiierten Ox. von Cumol>; | ||
Rk. mit dem Peroxy-Radikal von Styrol in EtOH bei 60grad <Inhibierung der durch Azoisobutyrodinitril initiierten Ox. von Styrol>; | ||
Rk.mit PbO2: ENDOR-Sp.; |
Rk. m. alkal. K3Fe(CN)6-Lsg. in Bzl. -> 2,6-Di-tert-butyl-<benzochinon-methyl-methid-(4)>; | ||
Rk. in 10-3 m benzol. Lsg. m. aktiv. PbO2 ->instabiles Radikal /BRN= 53907/ (X), durch EPR-Spektrum nachgewiesen; | ||
Zur Bildung v. Radikalen bei Rk. m. PbO2; | ||
Ox. m. K-ferricyanid/wss.NaOH -> 4-Ethyliden-2,6-di-t-butyl-cyclohexadien-(2,5)-on; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
at 17℃; Wasserstoff-Abstraktion; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Examples of alkylated monophenols of group a) are 2,6-di-tert-butyl-4-methylphenol, 2-tert-butyl-4,6-dimethylphenol, 2,6-di-tert-butyl-4-ethylphenol, 2,6-di-tert-butyl-4-n-butylphenol, 2,6-di-tert-butyl-4-isobutylphenol, 2,6-dicyclopentyl-4-methylphenol, 2-(α-methylcyclohexyl)-4,6-dimethylphenol, 2,6-dioctadecyl-4-methylphenol, 2,4,6-tricyclohexylphenol, 2,6-dinonyl-4-methylphenol, 2,4-dimethyl-6-(1'-methylundec-1'-yl)phenol, ... | ||
PHENOL COMPOUNDS OF GENERAL FORMULA (2) ... 2,6-di-tert-butylphenol, 2,4-di-tert-butylphenol, 2-tert-butyl-4-methoxyphenol, 2,4,6- trimethylphenol, 2,6-di-tert-butyl-4-ethylphenol, 2,4-dimethyl-6-tert-butylphenol, and 2,6-di-tert-butyl-4-hydroxytoluene 2,4,6-tri-tert-butylphenol. | ||
Alkylated Monophenols 2,6-Di-tert-butyl-4-methylphenol, 2,6-di-tert-butylphenol, 2-tert-butyl-4,6-dimethyl-phenol, 2,6-di-tert-butyl-4-ethyl-phenol, 2,6-di-tert-butyl-4-n-butylphenol, 2,6-di-tert-butyl-4-i-butylphenol, 2,6-di-cyclopentyl-4-methylphenol, 2-(β-methylcyclohexyl)-4,6-dimethylphenol, 2,6-di-octa-decyl-4-methylphenol, ... |
Alkylated Monophenols 2,6-Di-tert-butylphenol, 2,6-di-tert-butyl-4-methylphenol, 2,6-di-tert-butylphenol, 2-tert-butyl-4,6-dimethylphenol, 2,6-di-tert-butyl-4-ethylphenol, 2,6-di-tert-butyl-4-n-butylphenol, 2,6-di-tert-butyl-4-iso-butylphenol, 2,6-di-cyclopentyl-4-methylphenol, 2-(α-methylcyclohexyl)-4,6-dimethylphenol, ... | ||
Alkylated Monophenols 2,6-Di-tert-butyl-4-methylphenol, 2,6-di-tert-butylphenol, 2-tert-butyl-4,6-dimethylphenol, 2,6-di-tert-butyl-4-ethyl-phenol, 2,6-di-tert-butyl-4-n-butylphenol, 2,6-di-tert-butyl-4-i-butylphenol, 2,6-di-cyclopentyl-4-methylphenol, 2-(β-methylcyclohexyl)-4,6-dimethylphenol, 2,6-di-octa-decyl-4-methylphenol, ... | ||
Alkylated Monophenols 2,6-Di-tert.-butylphenol 2-tert.-Butyl-4,6-dimethylphenol 2,6-Di-tert.-butyl-4-ethylphenol 2,6-Di-tert.-butyl-4-n-butylphenol 2,6-Di-tert.-butyl-4-i-butylphenol 2,6-Di-cyclcopentyl-4-methylphenol 2-(β-Methylcyclohexyl)-4,6-dimethylphenol 2,6-Di-octadecyl-4-methylphenol 2,4,6-Tri-cyclohexylphenol ... | ||
Alkylated Monophenols 2,6-Di-tert.-butylphenol 2-tert.-butyl-4,6-dimethylphenol 2,6-di-tert.-butyl-4-ethylphenol 2,6-di-tert.-butyl-4-n-butylphenol 2,6-di-tert.-butyl-4-i-butylphenol 2,6-di-cyclcopentyl-4-methylphenol 2-(β-methylcyclohexyl)-4,6-dimethylphenol 2,6-di-octadecyl-4-methylphenol 2,4,6-tri-cyclohexylphenol ... | ||
Alkylated monophenols 2,6-Di-tert-butyl-4-methylphenol, 2,6-di-tert-butylphenol, 2-tert-butyl-4,6-dimethylphenol, 2,6-di-tert-butyl-4-ethylphenol, 2,6-di-tert-butyl-4-ethylphenol, 2,6-di-tert-butyl4-n-butylphenol, 2,6-di-tert-butyl-4-iso-butylphenol, 2,6-di-cyclopentyl-4-methylphenol, 2-(α-methylcyclohexyl)-4,6-dimethylphenol, ... | ||
Alkylated monophenols 2,6-Di-tert-butyl-4-methylphenol, 2,6-di-tert-butylphenol, 2-tert-butyl-4,6-dimethylphenol, 2,6-di-tert-butyl-4-ethylphenol, 2,6-di-tert-butyl-4-n-butylphenol, 2,6-di-tert-butyl-4-iso-butylphenol, 2,6-di-cyclopentyl-4-methylphenol, 2-(α-methylcyclohexyl)-4,6-dimethylphenol, 2,6-di-octadecyl-4-methylphenol, ... | ||
Alkylated Monophenols 2,6-di-tert.-butylphenol 2-tert.-butyl-4,6-dimethylphenol 2,6-Di-tert.-butyl-4-ethylphenol 2,6-Di-tert.-butyl-4-n-butylphenol 2,6-Di-tert.-butyl-4-i-butylphenol 2,6-Di-cyclopentyl-4-methylphenol 2-(α-Methylcyclohexyl)-4,6-dimethylphenol 2,6-Di-octadecyl-4-methylphenol 2,4,6-Tri-cyclohexylphenol ... | ||
Alkylated monophenols 2,6-di-tert-butylphenol 2-tert-butyl-4,6-dimethylphenol 2,6-di-tert-butyl-4-ethylphenol 2,6-di-tert-butyl-4-n-butylphenol 2,6-di-tert-butyl-4-i-butylphenol 2,6-dicyclopentyl-4-methylphenol 2-(α-methylcyclohexyl)-4,6-dimethylphenol 2,6-di-octadecyl-4-methylphenol 2,4,6-tricyclohexylphenol ... | ||
Alkylated monophenols 2,6-Di-tert-butyl-4-methylphenol, 2,6-di-tert-butylphenol, 2-tert-butyl-4,6-dimethylphenol, 2,6-di-tert-butyl-4-ethylphenol, 2,6-di-tert-butyl-4-n-butylphenol, 2,6-di-tert-butyl-4-isobutylphenol, 2,6-di-cyclopentyl-4-methylphenol, 2-(α-methylcyclohexyl)-4,6-dimethylphenol, 2,6-di-octadecyl-4-methylphenol, ... | ||
Alkylated monophenols 2,6-Di-tert-butyl-4-methylphenol 2,6-Di-tert-butylphenol 2-tert-Butyl-4,6-dimethylphenol 2,6-Di-tert-butyl-4-ethylphenol 2,6-Di-tert-butyl-4-n-butylphenol 2,6-Di-tert-butyl-4-iso-butylphenol 2,6-Di-cyclopentyl-4-methylphenol 2-(α-Methylcyclohexyl)-4,6-dimethylphenol 2,6-Di-octadecyl-4-methylphenol ... | ||
Alkylated Monophenols 2,6-Di-tert-butyl-4-methylphenol, 2,6-di-tert-butylphenol, 2-tert-butyl-4,6-dimethylphenol, 2,6-di-tert-butyl-4-ethylphenol, 2,6-di-tert-butyl-4-n-butylphenol, 2,6-di-tert-butyl-4-i-butylphenol, 2,6-di-cyclcopentyl-4-methylphenol, 2-(β-methylcyclohexyl)-4,6-dimethylphenol, 2,6-di-octadecyl-4-methylphenol, ... | ||
Alkylated Monophenols 2,6-Di-tert-butyl-4-methylphenol, 2,6-di-tert-butylphenol, 2-tert-butyl-4,6-dimethylphenol, 2,6-di-tert-butyl-4-ethyl-phenol, 2,6-di-tert-butyl-4-n-butylphenol, 2,6-di-tert-butyl- 4-i-butylphenol, 2,6-di-cyclopentyl-4-methylphenol, 2(β-methylcyclohexyl)4,6-dimethylphenol, 2,6-di-octa-decyl-4-methylphenol, ... | ||
Alkylated Monophenols 2,6-Di-tert-butyl-4-methylphenol, 2,6-di-tert-butylphenol, 2-tert-butyl-4,6-dimethylphenol, 2,6-di-tert-butyl-4-ethylphenol, 2,6-di-tert-butyl-4-n-butylphenol, 2,6-di-tertbutyl-4-i-butylphenol, 2,6-di-cyclopentyl-4-methylphenol, 2-(ß-methylcyclohexyl)4,6-di-methylphenol, 2,6-di-octadecyl-4-methylphenol, ... | ||
1. Alkylated Monophenols 2,6-Di-tert-butyl-4-methylphenol, 2,6-di-tert-butylphenol, 2-tert-butyl-4,6-dimethylphenol, 2,6-di-tert-butyl-4-ethylphenol, 2,6-di-tert-butyl-4-n-butylphenol, 2,6-di-tert-butyl-4-i-butylphenol, 2,6-di-cyclopentyl-4-methylphenol, 2-(β-methylcyclohexyl)-4,6-dimethylphenol, 2,6-di-octadecyl-4-methylphenol, ... | ||
Alkylated Monophenols 2,6-Di-tert.-butylphenol 2-tert.-butyl-4,6-dimethylphenol 2,6-di-tert.-butyl-4-ethylphenol 2,6-di-tert.-butyl-4-n-butylphenol 2,6-di-tert.-butyl-4-i-butylphenol ... |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
at 80 - 100℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | With nitrogen(II) oxide; sodium In methanol at 20℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 88 percent / Na; NO / methanol / 24 h / 20 °C / 1810.07 Torr 2: diethyl ether |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 88 percent / Na; NO / methanol / 24 h / 20 °C / 1810.07 Torr 2: diethyl ether |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 70 percent / O2, KOH / ethanol; H2O 2: 61 percent / NIS / acetonitrile / 0.17 h / 35 °C | ||
Multi-step reaction with 2 steps 1: SO2Cl2, PO(OMe)3 / 3 °C 2: 61 percent / NIS / acetonitrile / 0.17 h / 35 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: SO2Cl2, PO(OMe)3 / 3 °C 2: 37 percent / NIS / acetonitrile / 0.17 h / 35 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
62% | With O2 In dichloromethane mixt. was stirred with O2 bubbling at 0°C for 2-4 h; soln. was concd. in vac. below 20°C, light petroleum was added, soln. was allowed to stand in a refrigerator overnight, crystals were collected, washed with a mixt. of light petroleum and CH2Cl2, dried in vac.; elem. anal.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | With potassium hydroxide; Pd/C; zinc(II) oxide at 200℃; for 15h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 11.3% 2: 8% 3: 2% | With potassium hydroxide In ethanol at 230℃; for 0.333333h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 10 g 2: 3 g | With potassium hydroxide In ethanol at 230℃; for 0.5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydroxide at 220℃; for 5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | With bis-[(trifluoroacetoxy)iodo]benzene In 1,1,1,3',3',3'-hexafluoro-propanol at 0℃; for 0.0388889h; regioselective reaction; | |
70% | With bis-[(trifluoroacetoxy)iodo]benzene In 1,1,1,3',3',3'-hexafluoro-propanol |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | With perchloric acid; lead dioxide for 0.133333h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: sodium hydroxide; sodium hexacyanoferrate(II) decahydrate; sodium persulfate / water; hexane / 4 h / Inert atmosphere 2: caesium carbonate / dichloromethane / 12 h / 20 °C / Sealed tube |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: sodium hydroxide; sodium hexacyanoferrate(II) decahydrate; sodium peroxydisulfate / hexane; water / 4 h / Inert atmosphere 2: boron trifluoride diethyl etherate / dichloromethane / 10 h / 40 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
64% | With iodine In chloroform at 20℃; for 12h; regioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
58% | With iodine In chloroform at 20℃; for 12h; regioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
56% | With iodine In chloroform at 20℃; for 12h; regioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68% | With tert.-butylhydroperoxide; iodine In chloroform at 20℃; for 12h; regioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
47% | With tert.-butylhydroperoxide; iodine In chloroform at 20℃; for 12h; regioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With molybdenum(VI) oxide; In ethanol; at 280℃; for 4h;Inert atmosphere; | General procedure: 2.0 g of guaiac acid (purchased in Tianjin Guangfu Technology Co., Ltd.), 0.5 g of MOS catalyst and 100 ml of ethanol were placed in a 300 ml reaction vessel, and the air in the reaction vessel was replaced with nitrogen. The temperature was raised to 280 C, and the reaction was stirred for 4 h. After the reaction was completed, the mixture was filtered under suction and rotary evaporated. The liquid product was subjected to qualitative analysis on a gas chromatography-mass spectrometer (GC6890-MS5973, Agilent), and the internal standard was added. Quantitative analysis by gas chromatography. The chromatogram was performed on an HP-5ms, 30m X 0.25mm X 0.25mum capillary column. The conversion of the raw guaiacol is calculated by (initial guaiacol moles - residual guaiacol moles) / (initial guaiacol moles) X100%, and the selectivity of the product hydrocarbyl phenol is (hydrocarbyl phenol) The number of moles / (molar guaiacol moles) X 100 % was calculated. Among the guaiacol conversion products, ethyl phenols include o-ethyl phenol, 2,5-diethyl phenol, 3,5-diethyl phenol, and propyl phenols include 2,6-diisopropyl phenol. , 2,4-diisopropylphenol, 2,4,6-triisopropylphenol, butyl phenols including 2,5-di-sec-butylphenol, 2,6-di-tert-butylphenol, 2, 4-di-tert-butylphenol, 2,6-di-tert-butyl-p-ethylphenol, pentanols include 2,4-di-tert-amylphenol, others include o-ethoxyphenol, o-ethoxybenzene Methyl ether, p-ethyl guaiacol, 2,6-diisopropylanisole). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With molybdenum(VI) oxide; In ethanol; at 280℃; for 4h;Inert atmosphere; | General procedure: 2.0 g of guaiac acid (purchased in Tianjin Guangfu Technology Co., Ltd.), 0.5 g of MOS catalyst and 100 ml of ethanol were placed in a 300 ml reaction vessel, and the air in the reaction vessel was replaced with nitrogen. The temperature was raised to 280 C, and the reaction was stirred for 4 h. After the reaction was completed, the mixture was filtered under suction and rotary evaporated. The liquid product was subjected to qualitative analysis on a gas chromatography-mass spectrometer (GC6890-MS5973, Agilent), and the internal standard was added. Quantitative analysis by gas chromatography. The chromatogram was performed on an HP-5ms, 30m X 0.25mm X 0.25mum capillary column. The conversion of the raw guaiacol is calculated by (initial guaiacol moles - residual guaiacol moles) / (initial guaiacol moles) X100%, and the selectivity of the product hydrocarbyl phenol is (hydrocarbyl phenol) The number of moles / (molar guaiacol moles) X 100 % was calculated. Among the guaiacol conversion products, ethyl phenols include o-ethyl phenol, 2,5-diethyl phenol, 3,5-diethyl phenol, and propyl phenols include 2,6-diisopropyl phenol. , 2,4-diisopropylphenol, 2,4,6-triisopropylphenol, butyl phenols including 2,5-di-sec-butylphenol, 2,6-di-tert-butylphenol, 2, 4-di-tert-butylphenol, 2,6-di-tert-butyl-p-ethylphenol, pentanols include 2,4-di-tert-amylphenol, others include o-ethoxyphenol, o-ethoxybenzene Methyl ether, p-ethyl guaiacol, 2,6-diisopropylanisole). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With molybdenum(VI) oxide; In ethanol; at 280℃; for 4h;Inert atmosphere; | General procedure: 2.0 g of guaiac acid (purchased in Tianjin Guangfu Technology Co., Ltd.), 0.5 g of MOS catalyst and 100 ml of ethanol were placed in a 300 ml reaction vessel, and the air in the reaction vessel was replaced with nitrogen. The temperature was raised to 280 C, and the reaction was stirred for 4 h. After the reaction was completed, the mixture was filtered under suction and rotary evaporated. The liquid product was subjected to qualitative analysis on a gas chromatography-mass spectrometer (GC6890-MS5973, Agilent), and the internal standard was added. Quantitative analysis by gas chromatography. The chromatogram was performed on an HP-5ms, 30m X 0.25mm X 0.25mum capillary column. The conversion of the raw guaiacol is calculated by (initial guaiacol moles - residual guaiacol moles) / (initial guaiacol moles) X100%, and the selectivity of the product hydrocarbyl phenol is (hydrocarbyl phenol) The number of moles / (molar guaiacol moles) X 100 % was calculated. Among the guaiacol conversion products, ethyl phenols include o-ethyl phenol, 2,5-diethyl phenol, 3,5-diethyl phenol, and propyl phenols include 2,6-diisopropyl phenol. , 2,4-diisopropylphenol, 2,4,6-triisopropylphenol, butyl phenols including 2,5-di-sec-butylphenol, 2,6-di-tert-butylphenol, 2, 4-di-tert-butylphenol, 2,6-di-tert-butyl-p-ethylphenol, pentanols include 2,4-di-tert-amylphenol, others include o-ethoxyphenol, o-ethoxybenzene Methyl ether, p-ethyl guaiacol, 2,6-diisopropylanisole). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With molybdenum(VI) oxide; In ethanol; at 280℃; for 4h;Inert atmosphere;Catalytic behavior; | General procedure: 2.0 g of guaiac acid (purchased in Tianjin Guangfu Technology Co., Ltd.), 0.5 g of MOS catalyst and 100 ml of ethanol were placed in a 300 ml reaction vessel, and the air in the reaction vessel was replaced with nitrogen. The temperature was raised to 280 C, and the reaction was stirred for 4 h. After the reaction was completed, the mixture was filtered under suction and rotary evaporated. The liquid product was subjected to qualitative analysis on a gas chromatography-mass spectrometer (GC6890-MS5973, Agilent), and the internal standard was added. Quantitative analysis by gas chromatography. The chromatogram was performed on an HP-5ms, 30m X 0.25mm X 0.25mum capillary column. The conversion of the raw guaiacol is calculated by (initial guaiacol moles - residual guaiacol moles) / (initial guaiacol moles) X100%, and the selectivity of the product hydrocarbyl phenol is (hydrocarbyl phenol) The number of moles / (molar guaiacol moles) X 100 % was calculated. Among the guaiacol conversion products, ethyl phenols include o-ethyl phenol, 2,5-diethyl phenol, 3,5-diethyl phenol, and propyl phenols include 2,6-diisopropyl phenol. , 2,4-diisopropylphenol, 2,4,6-triisopropylphenol, butyl phenols including 2,5-di-sec-butylphenol, 2,6-di-tert-butylphenol, 2, 4-di-tert-butylphenol, 2,6-di-tert-butyl-p-ethylphenol, pentanols include 2,4-di-tert-amylphenol, others include o-ethoxyphenol, o-ethoxybenzene Methyl ether, p-ethyl guaiacol, 2,6-diisopropylanisole). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: water monomer; methanol / 3 h / 90 °C 2: palladium(0); hydrogen / 4 h / 140 °C | ||
Multi-step reaction with 2 steps 1: Aluminum Chloride / toluene / 0.25 h / -20 °C / Inert atmosphere 2: palladium 10% on activated carbon; hydrogen / ethanol / 2 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
225.37 g | With hydrogen; palladium at 140℃; for 4h; | 4 Add 2.5 g of palladium catalyst to a 1 L reactorAnd 270 g of 2,6-di-tert-butyl-4(dimethylaminoethyl)phenol solid,Then hydrogen is introduced, and the hydrogenolysis process maintains the system temperature at 140 ° C.The molar ratio of hydrogen to 2,6-di-tert-butyl-4(dimethylaminoethyl)phenol solid is 1.5:1,Hydrogenation reaction for 4 hours, hot filtration to remove the catalyst,Cooling and crystallization gave 225.37 g of 2,6-di-tert-butyl-p-ethylphenol. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
61% | With potassium fluoride; sodium azide; silver carbonate In N,N-dimethyl-formamide at 50℃; for 6h; | Typical synthetic procedure for compounds 3, 4 (with 3a asan example): General procedure: to a solution of phenylacetylene (1a)(0.055 mL, 0.5 mmol), 2,6-di-tert-butyl-4-methylphenol(BHT) (2a) (133 mg, 0.6 mmol), NaN3 (39 mg, 0.6 mmol)and KF (58 mg, 1.0 mmol) in DMF (1 mL) at 50 °C, Ag2CO3(41 mg, 0.15 mmol) was added. The reaction mixture wasthen stirred for 6 h when TLC conformed that substrate 1a was consumed. The resulting reaction mixture was cooled toroom temperature and extracted by dichloromethane(3×15 mL). The organic layer was washed with brine(3×40 mL), dried over MgSO4 and concentrated. Purificationof the crude product via flash column chromatography (silicagel; petroleum ether) and concentratinon in vacuo affordedthe desired product of 3a-N2/3a-N1 in 91% yield. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63% | With potassium fluoride; sodium azide; silver carbonate In N,N-dimethyl-formamide at 50℃; for 6h; | Typical synthetic procedure for compounds 3, 4 (with 3a asan example): General procedure: to a solution of phenylacetylene (1a)(0.055 mL, 0.5 mmol), 2,6-di-tert-butyl-4-methylphenol(BHT) (2a) (133 mg, 0.6 mmol), NaN3 (39 mg, 0.6 mmol)and KF (58 mg, 1.0 mmol) in DMF (1 mL) at 50 °C, Ag2CO3(41 mg, 0.15 mmol) was added. The reaction mixture wasthen stirred for 6 h when TLC conformed that substrate 1a was consumed. The resulting reaction mixture was cooled toroom temperature and extracted by dichloromethane(3×15 mL). The organic layer was washed with brine(3×40 mL), dried over MgSO4 and concentrated. Purificationof the crude product via flash column chromatography (silicagel; petroleum ether) and concentratinon in vacuo affordedthe desired product of 3a-N2/3a-N1 in 91% yield. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
18% | With 1,8-diazabicyclo[5.4.0]undec-7-ene; copper(ll) bromide In toluene at 20℃; for 1h; Inert atmosphere; | Typical experimental procedure for radical reactions General procedure: CuI (18.9 mg, 0.10 mmol), ligand (0.10 mmol), and 1 (1.0 mmol) were sequentially added under air to a dram vial equipped with a stir bar. 2 (1.0 mmol) and amine (2.0 mmol), and dried solvent (1.0 mL) were added by syringe, and the resulting mixture was vigorously stirred under nitrogen atmosphere [charged by general N2 (99.95%) gas flow] for 1 h at room temperature, as shown in the tables. After this time, the contents of the flask were filtered through a plug of silica gel and then concentrated by rotary evaporation. The residue was purified by flash chromatography, eluting with hexane/EtOAc to afford the product 3. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With copper(l) iodide; 1,8-diazabicyclo[5.4.0]undec-7-ene; 4,4'-di-tert-butyl-2,2'-bipyridine In toluene at 20℃; for 20h; Inert atmosphere; | Typical experimental procedure for radical reactions General procedure: CuI (18.9 mg, 0.10 mmol), ligand (0.10 mmol), and 1 (1.0 mmol) were sequentially added under air to a dram vial equipped with a stir bar. 2 (1.0 mmol) and amine (2.0 mmol), and dried solvent (1.0 mL) were added by syringe, and the resulting mixture was vigorously stirred under nitrogen atmosphere [charged by general N2 (99.95%) gas flow] for 1 h at room temperature, as shown in the tables. After this time, the contents of the flask were filtered through a plug of silica gel and then concentrated by rotary evaporation. The residue was purified by flash chromatography, eluting with hexane/EtOAc to afford the product 3. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | With copper(l) iodide; 1,8-diazabicyclo[5.4.0]undec-7-ene; 4,4'-di-tert-butyl-2,2'-bipyridine In toluene at 20℃; for 1h; Inert atmosphere; | Typical experimental procedure for radical reactions General procedure: CuI (18.9 mg, 0.10 mmol), ligand (0.10 mmol), and 1 (1.0 mmol) were sequentially added under air to a dram vial equipped with a stir bar. 2 (1.0 mmol) and amine (2.0 mmol), and dried solvent (1.0 mL) were added by syringe, and the resulting mixture was vigorously stirred under nitrogen atmosphere [charged by general N2 (99.95%) gas flow] for 1 h at room temperature, as shown in the tables. After this time, the contents of the flask were filtered through a plug of silica gel and then concentrated by rotary evaporation. The residue was purified by flash chromatography, eluting with hexane/EtOAc to afford the product 3. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With copper(l) iodide; 1,8-diazabicyclo[5.4.0]undec-7-ene; 4,4'-di-tert-butyl-2,2'-bipyridine In toluene at 20℃; for 1h; Inert atmosphere; | Typical experimental procedure for radical reactions General procedure: CuI (18.9 mg, 0.10 mmol), ligand (0.10 mmol), and 1 (1.0 mmol) were sequentially added under air to a dram vial equipped with a stir bar. 2 (1.0 mmol) and amine (2.0 mmol), and dried solvent (1.0 mL) were added by syringe, and the resulting mixture was vigorously stirred under nitrogen atmosphere [charged by general N2 (99.95%) gas flow] for 1 h at room temperature, as shown in the tables. After this time, the contents of the flask were filtered through a plug of silica gel and then concentrated by rotary evaporation. The residue was purified by flash chromatography, eluting with hexane/EtOAc to afford the product 3. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | With copper(l) iodide; 1,8-diazabicyclo[5.4.0]undec-7-ene; 4,4'-di-tert-butyl-2,2'-bipyridine In toluene at 20℃; for 20h; Inert atmosphere; | Typical experimental procedure for radical reactions General procedure: CuI (18.9 mg, 0.10 mmol), ligand (0.10 mmol), and 1 (1.0 mmol) were sequentially added under air to a dram vial equipped with a stir bar. 2 (1.0 mmol) and amine (2.0 mmol), and dried solvent (1.0 mL) were added by syringe, and the resulting mixture was vigorously stirred under nitrogen atmosphere [charged by general N2 (99.95%) gas flow] for 1 h at room temperature, as shown in the tables. After this time, the contents of the flask were filtered through a plug of silica gel and then concentrated by rotary evaporation. The residue was purified by flash chromatography, eluting with hexane/EtOAc to afford the product 3. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With perrhenic acid anhydride; at 320℃; for 6h;Inert atmosphere; Sealed tube; | General procedure: The catalytic reactions were carried out in a batch reactor (ParrInstruments, 300 mL). In a typical model compound conversion experiment,the reactor was loaded with 0.1 g catalyst, 1 g substrate,60 mL solvent, sealed and purged with N2 five times. The reactor wasthen heated to the desired reaction temperature within 1.5 h and kept atthis temperature for the desired reaction time with stirring at 550 rpm.The reaction time was denoted as 0 h when the prescribed reactiontemperature was reached. After the reaction, the reactor was firstlycooled in air by removing the heating jacket. On reaching below 150 C,the reactor was further cooled by immersing it into cold-water. Thepost-reaction solution and the spent catalyst were separated by filtration.The solution mixture was analyzed with an Agilent Technologies6890 N gas chromatograph (GC) equipped with a HP-5 MS capillarycolumn (Agilent, 30m ×0.25mm ×0.25 mum) and a FID detector withanisole as the internal standard. However, when the substrate was anisole,tridecane was chosen as the internal standard. The GC parameterswere: inlet temperature 280 C, detector temperature 300 C, split ratio1:50. The oven temperature ramped from 45 C to 105 C at 15 Cmin-1, and then ramped to 280 C at 6 C min-1. Products wereidentified with a gas chromatograph-mass spectroscopy (GC-MS,Agilent Technologies, model 5973). The mass spectrum acquired withthe GC-MS was retrieved in the NIST Mass Spectral Library to identifythe structure of each product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In toluene Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: potassium hexacyanoferrate(III); potassium hydroxide / water / 1 h / 23 °C / Inert atmosphere 2: tetrabutylammomium bromide / water / 80 °C / Green chemistry |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77% | With sodium hypochlorite pentahydrate; tetra-(n-butyl)ammonium iodide In ethyl acetate at 25℃; for 0.5h; Green chemistry; chemoselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In 5,5-dimethyl-1,3-cyclohexadiene at 140℃; for 2h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: 5,5-dimethyl-1,3-cyclohexadiene / 2 h / 140 °C / Inert atmosphere 2.1: triethylamine; 4-toluenesulfonyl azide / acetonitrile / 20 h / 20 °C / Inert atmosphere 2.2: 4 h / Inert atmosphere 3.1: tetrakis(acetonitrile)copper(I)tetrafluoroborate; N,N'-(ethane-1,2-diyl)bis(1-(2,6-dichlorophenyl)methanimine) / 1,2-dichloro-ethane / 50 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: 5,5-dimethyl-1,3-cyclohexadiene / 2 h / 140 °C / Inert atmosphere 2.1: triethylamine; 4-toluenesulfonyl azide / acetonitrile / 20 h / 20 °C / Inert atmosphere 2.2: 4 h / Inert atmosphere 3.1: tetrakis(acetonitrile)copper(I)tetrafluoroborate; N,N'-(ethane-1,2-diyl)bis(1-(2,6-dichlorophenyl)methanimine) / 1,2-dichloro-ethane / 50 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: 5,5-dimethyl-1,3-cyclohexadiene / 2 h / 140 °C / Inert atmosphere 2.1: triethylamine; 4-toluenesulfonyl azide / acetonitrile / 20 h / 20 °C / Inert atmosphere 2.2: 4 h / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: potassium hydroxide; potassium hexacyanoferrate(III) / hexane; water / 1 h / 20 °C 2: diethylzinc / tetrahydrofuran / 0.25 h / 20 °C / Schlenk technique; Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium hydroxide; potassium hexacyanoferrate(III) In hexane; water at 20℃; for 1h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
49% | With [CuII(η1-O2•−)(tris(5-(2,4,6-triphenylbenzene)-2-pyridylmethyl)amine)]+ In tetrahydrofuran at -40℃; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
15% | With air at 20℃; for 3h; Irradiation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With palladium 10% on activated carbon; hydrogen In ethanol at 20℃; for 2h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: potassium hexacyanoferrate(III); potassium hydroxide / water monomer; hexane / 1 h / 23 °C / Inert atmosphere 2: 1,8-diazabicyclo[5.4.0]undec-7-ene / tert-butyl methyl ether / 0.5 h / 20 °C / Inert atmosphere |
Tags: 4130-42-1 synthesis path| 4130-42-1 SDS| 4130-42-1 COA| 4130-42-1 purity| 4130-42-1 application| 4130-42-1 NMR| 4130-42-1 COA| 4130-42-1 structure
[ 1879-09-0 ]
2-(tert-Butyl)-4,6-dimethylphenol
Similarity: 1.00
[ 57354-65-1 ]
4-(tert-Butyl)-2,6-diisopropylphenol
Similarity: 1.00
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